How much have you invested for the financial side of your retirement?

How about the non-financial side?

Join us for six Fridays starting on October 3rd and get moving on your roadmap.

Learn more here.

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Transitions are rarely easy, whether you’re leaving your career or any other life chapter that has helped define you. Cassidy Krug knows this firsthand. A 2012 Olympian in diving, she grew up immersed in the sport—coached by her parents, competing at Stanford, and training for years beyond. When she reached her dream of competing at the London Games, she also knew it was time to move on.

In this conversation, Cassidy Krug shares the lessons she learned about navigating major life transitions—from sport to career, and from an “all-in” life to an “à la carte” one. She talks candidly about the identity shifts, the uncertainty of new beginnings, and the importance of reflection, interpretation, and community. Her story offers inspiration and practical wisdom for anyone facing their own turning points, especially those contemplating or entering retirement.

Cassidy Krug joins us from Los Angeles.

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We Discuss

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Bio 

Cassidy Krug is the author of Resurface: A Guide to Navigating Life’s Biggest Transitions. She is a former Olympic diver, a writer, and a brand and innovation strategist based in Los Angeles. She graduated from Stanford with an English degree and she won two NCAA diving titles there.

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For More on Cassidy Krug

Resurface: A Guide to Navigating Life’s Biggest Transitions

Website

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Podcast Conversations You May Like

The Portfolio Life – Christina Wallace

Strategic Quitting – Julia Keller

Edit Your Life – Elisabeth Sharp McKetta

The Skill Set for Life’s Transitions – Bruce Feiler

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There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time.

About Retirement Wisdom

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.

Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.

Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University.

In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 1.6 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

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Wise Quotes

On Transitions

“Change is something that happens to you. Transition is how you choose to react to that change. But the real work is in interpretation—deciding how you want to remember and carry that story forward.”

On Redefining Success

“First of all, just by asking the question, what does success look like for me? What do I want in my retirement? And it’s not going to be a status quo answer that’s given to you by your career. Maybe for a very long time, you wanted to get the next promotion to get the next pay raise, or to have more responsibility. And all of a sudden, like that ladder is gone and you ask yourself, what does success look like for me now? Maybe success looks like showing up as well as I can and having a positive impact on my family. Maybe success looks like finding people who are still in the workforce and mentoring them and helping them to guide them to make the right decisions. Maybe success looks like making an impact in a totally different sphere, but bringing all the skills that I learned in the workplace to a non-profit or to a different arena. But you really do have to sit and reflect and ask that question of yourself and not expect that the world is necessarily going to tell you anymore what it means to live a successful life.”

On Quitting

“Every time I’ve quit something, it’s directed my life in ways I didn’t see coming—and that I’m immensely grateful for.”

On Moving Forward

“Don’t try to replace what you’re leaving behind. Honor it. Then look for the pieces you loved and carry them into your next chapter.”

On Interpreting Your Story

“And for me, I choose to think back on the Olympic experience as one that I’m really proud of, rather than one that I messed up and I’m regretful for. Absolutely, it takes choice. It takes a lot of reflection. It takes taking the first swell of emotions, whatever that might be, and questioning it, and looking at  from a broader perspective with a longer lens, but I do think that we,  always have a choice in how we interpret our own stories.  And I think it’s so important to get that right according to how we want to feel about ourselves.”

On Trying New Things…and an à la carte life

“..at first it’s scary because when you have an all-in-one life, so many decisions are made for you. So many choices are just obvious because you have only one thing at the middle. And so when you don’t anymore, the balancing of things, the trying to decide what the right path is, you have all those questions more often. But I think answering those kind of questions constantly –  Am I doing what I want to do? Am I being fulfilled? How do I shift maybe some time and energy away from this and into this other thing? That’s been such a fulfilling part of what my life has been since I started living this à la carte life. In general, I don’t love trying new things. I love being good at things. And so it’s always hard to put myself in that situation where I don’t feel the same level of accomplishment as I did when I was the best in the world diver. That said, for me, once I get into them a little bit, so once, you’re in day two, day three, day four, once I started trapeze and started to feel the process of learning and growing and was exploring new sides of myself, then it grew into a passion for me.”